Anyhow, I thought I'd relate my own experience and give my current two cents on the topic of building a lolita wardrobe. I'm still a relative newbie to the fashion, and I'm sure that if I stick with lolita for a few more years my opinions will change at least a little bit. But at this point my attitude is really very simple; provided it's not going to mean you can't buy food or fuel, build up your wardrobe in whatever manner will make you happiest.
For myself, I was lucky enough that my awesome man bought em a pretty complete wardrobe right off the bat and it's been fantastic. However, the only downside of being able to get a fair bit of gear straight off is you can make some bad choices because, as always when buying clothes online, you aren't going to know how things are going to look and what you're going to like until you have it, and if you buy five dresses at once straight away, chances are they might not all work for you. So my advice on that front is to take it slow, even if you do have the means to buy your complete starting wardrobe all at once. Buy one complete outfit, perhaps with a few variables such a different socks or blouses see what works for you in it, and then go on from there.
When I sit down and think about it, things like budget and personal taste aside, I think there are three golden rules to keep in mind when building your lolita wardrobe.
Basics really are that important.
Everyone says it, and now I'm saying it. Lolita needs a petticoat. Without a petti, you just have a very cute outfit that's not quite lolita. However, I'm going to go against common wisdom and say that, right at the beginning, you don't necessarily need a great petti. My first one was a Leg Avenue tutu, and it was alright, and it was a good $30 cheaper than my Classical Puppets one. Unless you absolutely know for sure you want to wear lolita, and I'm very impressed if you do and I'd also like to ask you for next week's lottery numbers, as cheaper petticoat will be good enough for you to test the lolita fashion waters with.
It's fluffy enough ^__^
To me basics also covers more than just petticoat - it means shoes, socks and something to put on your head. Knee high socks, mary janes and a headbow of some kind are such typically lolita accessories that they should be part of your first outfit. There will be time to get experimental later.
Now, you may be wondering why I haven't mentioned bloomers as a basic wardrobe item. Though I know modesty is a lolita virtue, to me bloomers are underwear, and I think I have no right to tell anyone what underwear they should wear. Yes, bloomers protect you in the case of winds from having people see your panties, but they aren't essential.
Avoid things you hate.
I have never been able to wear big things on my head. Small clips, fancy hair ties, plain headbands, little bows and full size hats have always been fine. Then I enter the lolita scene and everything is headeating bows. So I try headeating bows, and feel uncomfortable and look it. The lesson in that is simple. If you don't like something normally, or something doesn't look good on your normally, you probably won't like it any more and it won't look any better just by virtue of being part of a lolita coord.
Fortunately, the reverse is also true! If you look great in blue normally, you're going to look great in that colour in lolita. As long as you adhere to the lolita aesthetic and silhouette, I tihnk its most important to wear things that are flattering and make you feel comfortable. Lolita is a fashion, not a costume, and you should never wear anything that makes you feel like it's a costume, and whatever that is is personal. For me, it's headeating bows ^__^
Find the right blouse.
This may be an odd bit of advice, but its one I've found works for me. Discover your perfect blouse...and then get five of it! Well, it doesn't have to be five exactly, but once you find a blouse that looks good and feels comfortable, try and get it in as many colours as you'd use, and perhaps buy two in whatever colour you'd use most, like white or black. A flattering blouse is important - you can have lots of lovely skirts and JSKs but without the right blouse you don't have the right outfit.
This may sound like it will be limiting your outfits by wearing the same style blouse frequently, so all I will do it point you to the tumblr of a wonderful sweet lolita, Cadney. If you browse through her outfit photos you'll notice that she has the Bodyline L364 in several colours, and she uses it very well in range of different outfits in a variety of colours.
Of course, I'm not saying stick to only one blouse, but I do suggest that when you find one that works well for you that you do get a few of it if that's at all possible. If I'm being totally honest, my next Bodyline order I'm saving for is going to be just that - repeats of the blouses I have found I like best ^__^
Now, if you are a regular reader of my blog, you'd have seen my hypothetical wardrobe posts where I build imaginary lolita wardrobes in the various style and substyles. However, this post and those are different kettles of fish. Those are my thoughts on how you could build a specific wardrobe, on a budget, to fit a particular style. This is about my thoughts on building a lolita wardrobe in general, and, since this article is already long enough, I shall end it here ^__^